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      Anthraquinones with Antiplasmodial Activity from the Roots of Rennellia elliptica Korth. (Rubiaceae)

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          Abstract

          Dichloromethane root extract of Rennellia elliptica Korth. showed strong inhibition of Plasmodium falciparum growth in vitro with an IC 50 value of 4.04 µg/mL. A phytochemical study of the dichloromethane root extract has led to the isolation and characterization of a new anthraquinone, 1,2-dimethoxy-6-methyl-9,10-anthraquinone ( 1), and ten known anthraquinones: 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone ( 2), nordamnacanthal ( 3), 2-formyl-3-hydroxy-9,10-anthraquinone ( 4), damnacanthal ( 5), lucidin- ω-methyl ether ( 6), 3-hydroxy-2-methyl-9,10-anthraquinone ( 7), rubiadin ( 8), 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone ( 9), rubiadin-1-methyl ether ( 10) and 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone ( 11). Structural elucidation of all compounds was accomplished by modern spectroscopic methods, notably 1D and 2D NMR, IR, UV and HREIMS. The new anthraquinone 1, 2-formyl-3-hydroxy-9,10-anthraquinone ( 4) and 3-hydroxy-2-methyl-9,10-anthraquinone ( 7) possess strong antiplasmodial activity, with IC 50 values of 1.10, 0.63 and 0.34 µM, respectively.

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          Most cited references 23

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          Biological activity of Anthraquinones and Triterpenoids from Prismatomeris fragrans.

          A new 1,3-dihydroxy-2-methyl-5,6-dimethoxyanthraquinone (1); six known anthraquinones, nordamnacanthal (2), damnacanthal (3), rubiadin (4), rubiadin-1-methyl ether (5), lucidin-omega-methyl ether (6), and 1-hydroxy-2-hydroxymethyl-3-methoxyanthraquinone (7); a beta-sitosterol (8); together with two known triterpenoids, beta-acetylolean-12-en-28-olic acid (9), and 3beta-O-acetyl-11alpha,12alpha-epoxyolean-28,13-olide (10) were isolated from the roots and stems of Prismatomeris fragrans. Their structures were established on the basis of spectral data. This is the first isolation of compounds 2, 6, 7, 9 and 10 from Prismatomeris genus. The isolated compounds were evaluated in antiplasmodial, antituberculosis, antifungal and anticancer cell lines tests. The bioactivity assays showed that only 9 exhibited moderate antimalarial activity, 2 and 3 exhibited antifungal activity while 2, 3, 4, 7 and 9 showed antituberculosis activity. In addition, compounds 2, 3 and 7 exhibited cytotoxicity to BC cell line while 1, 1a (the methyl ether derivative of 1), 2, 3, 4, 5, and 9 exhibited cytotoxicity to NCI-H187 cell line.
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            Phylogeny and classification of the subfamily Rubioideae (Rubiaceae)

             J Manen,  B Bremer (2000)
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              Structure-activity studies: in vitro antileishmanial and antimalarial activities of anthraquinones from Morinda lucida.

              Anthraquinones have been isolated by bioassay-guided fractionation from Morinda lucida. Structure-activity studies show that an aldehyde group at C-2 and a phenolic hydroxy group at C-3 enhance the activity of the anthraquinones against the growth of Plasmodium falciparum and promastigotes of Leishmania major in vitro.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                20 October 2010
                October 2010
                : 15
                : 10
                : 7218-7226
                Affiliations
                [1 ]Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
                [2 ]Centre for Natural Product Research and Drug Discovery (CENAR), Chemistry Department, Faculty of Science, Universiti Malaya, 50603 Kuala Lumpur, Malaysia
                Author notes
                [* ] Author to whom correspondence should be addressed; E-Mail: norhadiani@ 123456salam.uitm.edu.my ; Tel.: +603-55444591.
                Article
                molecules-15-07218
                10.3390/molecules15107218
                6259154
                20966871
                © 2010 by the authors;

                licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

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